Azocyclotin
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Basic Info
| Common Name | Azocyclotin(F04165) |
| 2D Structure | |
| Description | Azocyclotin is an organotin compound. Tin is a chemical element with the symbol Sn and atomic number 50. It is a natural component of the earth's crust and is obtained chiefly from the mineral cassiterite, where it occurs as tin dioxide. (L307, L309) |
| FRCD ID | F04165 |
| CAS Number | 41083-11-8 |
| PubChem CID | 91634 |
| Formula | C20H35N3Sn |
| IUPAC Name | tricyclohexyl(1,2,4-triazol-1-yl)stannane |
| InChI Key | ONHBDDJJTDTLIR-UHFFFAOYSA-N |
| InChI | InChI=1S/3C6H11.C2H2N3.Sn/c3*1-2-4-6-5-3-1;1-3-2-5-4-1;/h3*1H,2-6H2;1-2H;/q;;;-1;+1 |
| Canonical SMILES | C1CCC(CC1)[Sn](C2CCCCC2)(C3CCCCC3)N4C=NC=N4 |
| Isomeric SMILES | C1CCC(CC1)[Sn](C2CCCCC2)(C3CCCCC3)N4C=NC=N4 |
| Synonyms |
Peropal
(1H-1,2,4-Triazolyl)tricyclohexylstannane
Azocyclotin
41083-11-8
1-(Tricyclohexylstannyl)-1H-1,2,4-triazole
BAY bue 1452
Azocyclotin [BSI:ISO]
UNII-V4YRQ367KE
HSDB 6559
Tri(cyclohexyl)-1H-1,2,4-triazol-1-yltin
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Azoles |
| Subclass | Triazoles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Triazoles |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Heteroaromatic compound - 1,2,4-triazole - Trialkyltin - Azacycle - Organic metal salt - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organic tin salt - Organic salt - Organotin compound - Organonitrogen compound - Organometallic compound - Organic post-transition metal moeity - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as triazoles. These are compounds containing a five-member aromatic ring of two carbon atoms and three nitrogen atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 436.231 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Complexity | 339 |
| Monoisotopic Mass | 437.185 |
| Exact Mass | 437.185 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9662 |
| Human Intestinal Absorption | HIA+ | 0.8687 |
| Caco-2 Permeability | Caco2+ | 0.5000 |
| P-glycoprotein Substrate | Non-substrate | 0.6948 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8122 |
| Non-inhibitor | 0.9370 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.5794 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5611 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7568 |
| CYP450 2D6 Substrate | Non-substrate | 0.8501 |
| CYP450 3A4 Substrate | Non-substrate | 0.6801 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7869 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7944 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8042 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5527 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5097 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6409 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8446 |
| Non-inhibitor | 0.7527 | |
| AMES Toxicity | AMES toxic | 0.5134 |
| Carcinogens | Non-carcinogens | 0.9081 |
| Fish Toxicity | High FHMT | 0.9931 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9539 |
| Honey Bee Toxicity | Low HBT | 0.7583 |
| Biodegradation | Not ready biodegradable | 0.9223 |
| Acute Oral Toxicity | III | 0.6553 |
| Carcinogenicity (Three-class) | Non-required | 0.3673 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.0159 | LogS |
| Caco-2 Permeability | 1.0165 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2182 | LD50, mol/kg |
| Fish Toxicity | 1.1213 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7211 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicity of Three Acaricides to the Predatory Mite, Neoseiulus bicaudus (Acari: Phytoseiidae) and Their Impact on the Functional Response to Tetranychus turkestani (Acari: Tetranychidae). | J Econ Entomol | 2017 Oct 1 | 28962002 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
- Gene Name:
- ADH5
- Uniprot ID:
- P11766
- Molecular Weight:
- 39723.945 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Threonine-type endopeptidase activity
- Specific Function:
- The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly basic pH. The proteasome has an ATP-dependent proteolytic activity. This unit is responsible of the chymotrypsin-like activity of the proteasome and is one of the principal target of the proteasome inhibitor bortezomib. May catalyze basal processing of intracellular antigens. Plays a role in the protection against oxidative damage through the Nrf2-ARE pathway (By similarity).
- Gene Name:
- PSMB5
- Uniprot ID:
- P28074
- Molecular Weight:
- 28480.01 Da
- Mechanism of Action:
- Organotins inhibit the chymotrypsin-like activity of 20S and cellular proteasomes by binding to the beta-5 subunit. This results in apoptosis caused by downstream effects in the proteasome pathway.
References
- Shi G, Chen D, Zhai G, Chen MS, Cui QC, Zhou Q, He B, Dou QP, Jiang G: The proteasome is a molecular target of environmental toxic organotins. Environ Health Perspect. 2009 Mar;117(3):379-86. doi: 10.1289/ehp.11865. Epub 2008 Oct 23. [19337512 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of hormone ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function.
- Gene Name:
- RARB
- Uniprot ID:
- P10826
- Molecular Weight:
- 50488.63 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of retinoic acid receptors, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity).
- Gene Name:
- RARG
- Uniprot ID:
- P13631
- Molecular Weight:
- 50341.405 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of retinoic acid receptors, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH1A
- Uniprot ID:
- P07327
- Molecular Weight:
- 39858.37 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH1B
- Uniprot ID:
- P00325
- Molecular Weight:
- 39854.21 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH1C
- Uniprot ID:
- P00326
- Molecular Weight:
- 39867.27 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH4
- Uniprot ID:
- P08319
- Molecular Weight:
- 40221.335 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ADH6
- Uniprot ID:
- P28332
- Molecular Weight:
- 39088.335 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
- Gene Name:
- ADH7
- Uniprot ID:
- P40394
- Molecular Weight:
- 41480.985 Da
- Mechanism of Action:
- Inorganic and organic tin compounds are weak inhibitors of alcohol dehydrogenase.
References
- Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of peroxisome proliferator-activated receptor gamma, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
- Gene Name:
- RARA
- Uniprot ID:
- P10276
- Molecular Weight:
- 50770.805 Da
- Mechanism of Action:
- Organotins are endocrine disruptors and are believed to contribute to obesity by inappropriate activation of retinoic acid receptors, leading to adipocyte differentiation.
References
- Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]